(1S,2S,5R,6S,9S,12S,15R,16S,21R)-6,16-dihydroxy-5,15-dimethyl-8,13,17-trioxahexacyclo[14.2.2.11,12.02,10.05,9.015,21]henicos-10-en-14-one

Details

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Internal ID 91949a43-edae-4b85-a52d-a2ea7c9dd018
Taxonomy Organoheterocyclic compounds > Naphthopyrans
IUPAC Name (1S,2S,5R,6S,9S,12S,15R,16S,21R)-6,16-dihydroxy-5,15-dimethyl-8,13,17-trioxahexacyclo[14.2.2.11,12.02,10.05,9.015,21]henicos-10-en-14-one
SMILES (Canonical) CC12CCC3C(=CC4C5C36CCC(C5(C(=O)O4)C)(OC6)O)C1OCC2O
SMILES (Isomeric) C[C@]12CC[C@@H]3C(=C[C@H]4[C@@H]5[C@]36CC[C@@]([C@@]5(C(=O)O4)C)(OC6)O)[C@@H]1OC[C@H]2O
InChI InChI=1S/C20H26O6/c1-17-4-3-11-10(15(17)24-8-13(17)21)7-12-14-18(2,16(22)26-12)20(23)6-5-19(11,14)9-25-20/h7,11-15,21,23H,3-6,8-9H2,1-2H3/t11-,12+,13-,14+,15+,17-,18+,19+,20+/m1/s1
InChI Key AWXCFXSOVHMZKV-DSMHVVIASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H26O6
Molecular Weight 362.40 g/mol
Exact Mass 362.17293854 g/mol
Topological Polar Surface Area (TPSA) 85.20 Ų
XlogP 0.20
Atomic LogP (AlogP) 1.15
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 0

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,2S,5R,6S,9S,12S,15R,16S,21R)-6,16-dihydroxy-5,15-dimethyl-8,13,17-trioxahexacyclo[14.2.2.11,12.02,10.05,9.015,21]henicos-10-en-14-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9738 97.38%
Caco-2 + 0.5604 56.04%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.8607 86.07%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9000 90.00%
OATP1B3 inhibitior + 0.9663 96.63%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6201 62.01%
BSEP inhibitior - 0.5344 53.44%
P-glycoprotein inhibitior - 0.8074 80.74%
P-glycoprotein substrate - 0.5309 53.09%
CYP3A4 substrate + 0.6822 68.22%
CYP2C9 substrate - 0.8070 80.70%
CYP2D6 substrate - 0.8401 84.01%
CYP3A4 inhibition - 0.9048 90.48%
CYP2C9 inhibition - 0.9498 94.98%
CYP2C19 inhibition - 0.9477 94.77%
CYP2D6 inhibition - 0.9301 93.01%
CYP1A2 inhibition - 0.8859 88.59%
CYP2C8 inhibition - 0.7496 74.96%
CYP inhibitory promiscuity - 0.9670 96.70%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Danger 0.4336 43.36%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.9807 98.07%
Skin irritation + 0.5501 55.01%
Skin corrosion - 0.9341 93.41%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6834 68.34%
Micronuclear - 0.8800 88.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.9005 90.05%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity - 0.5888 58.88%
Acute Oral Toxicity (c) III 0.4097 40.97%
Estrogen receptor binding + 0.8709 87.09%
Androgen receptor binding + 0.6641 66.41%
Thyroid receptor binding + 0.6690 66.90%
Glucocorticoid receptor binding + 0.8503 85.03%
Aromatase binding + 0.7013 70.13%
PPAR gamma + 0.5884 58.84%
Honey bee toxicity - 0.8104 81.04%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9648 96.48%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.76% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.24% 100.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.71% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.77% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.10% 95.56%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 88.67% 82.69%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.48% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.33% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.77% 97.25%
CHEMBL3922 P50579 Methionine aminopeptidase 2 85.77% 97.28%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.76% 99.23%
CHEMBL2581 P07339 Cathepsin D 85.05% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.03% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.99% 95.89%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.17% 93.03%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Casimirella ampla

Cross-Links

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PubChem 162889831
LOTUS LTS0192745
wikiData Q104920351